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Title
Japanese: 
English:Boron-mediated sequential alkyne insertion and C–C coupling reactions affording extended π-conjugated molecules 
Author
Japanese: 庄子良晃, 田中直樹, 村中翔, 滋野直樹, 杉山陽香, 竹ノ内 久美子, Fatin Hajjaj, 福島孝典.  
English: Yoshiaki Shoji, Naoki Tanaka, Sho Muranaka, Naoki Shigeno, Haruka Sugiyama, Kumiko Takenouchi, Fatin Hajjaj, Takanori Fukushima.  
Language English 
Journal/Book name
Japanese: 
English:Nature Communications 
Volume, Number, Page Vol. 7        p. 12704
Published date Sept. 2016 
Publisher
Japanese: 
English:Macmillan Publishers Limited 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL http://www.nature.com/articles/ncomms12704
 
DOI https://doi.org/10.1038/ncomms12704
Abstract C–C bond coupling reactions illustrate the wealth of organic transformations, which are usually mediated by organotransition metal complexes. Here, we show that a borafluorene with a B–Cl moiety can mediate sequential alkyne insertion (1,2-carboboration) and deborylation/Csp2–Csp2 coupling reactions, leading to aromatic molecules. The first step, which affords a borepin derivative, proceeds very efficiently between the borafluorene and various alkynes by simply mixing these two components. The second step is triggered by a one-electron oxidation of the borepin derivative, which results in the formation of a phenanthrene framework. When an excess amount of oxidant is used in the second step, the phenanthrene derivatives can be further transformed in situ to afford dibenzo[g,p]chrysene derivatives. The results presented herein will substantially expand the understanding of main group chemistry and provide a powerful synthetic tool for the construction of a wide variety of extended π-conjugated systems.

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